| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,586.22 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $11,515.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,735.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,720.00 | Reimagined |
| 2020 | $800.00 | Wellesley to Wellesley (50 mile Sunday) |
| 1993 | $0.00 | PMC Rider |
